Reacción #310095

Ecuación de reacción

NH4Cl

Compound 3

Methyl 3-cyano-4-hydroxybenzoate

chloroiodomethane

NH4OH

diethyl zinc

→

compound 4

Rendimiento 30.0%

Methyl 3-cyano-4-isopropoxybenzoate

Rendimiento 30.0%

Disolventes

EtOAc

1,2-dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm to room temperature
2. 2
   TemperaturaIt was again cooled to 0° C. with an ice bath
3. 3
   OtroThe layers were separated
4. 4
   Extracciónthe aqueous phase was extracted with additional EtOAc (2×100 mL)
5. 5
   Secadodried (Na2SO4)
6. 6
   Concentraciónconcentrated to a crude oil which
7. 7
   Otrowas purified over silica gel (100% hexanes)

Procedimiento

Compound 3 (5.56 g, 24.0 mmol) was added to a solution of chloroiodomethane (5.59 mL, 76.8 mmol) in 1,2-dichloroethane (35 mL) under an atmosphere of nitrogen. The solution was cooled to 0° C. with an ice bath and diethyl zinc (38.4 mL, 1.0 M in hexanes, 38.4 mmol) was added over 10 minutes. The resulting mixture was stirred for 30 minutes and allowed to warm to room temperature. It was again cooled to 0° C. with an ice bath, and saturated aqueous NH4Cl (150 mL) was added, followed by concentrated aqueous NH4OH (25 mL) and EtOAc (200 mL). The layers were separated and the aqueous phase was extracted with additional EtOAc (2×100 mL). The organic phases were combined, dried (Na2SO4) and concentrated to a crude oil which was purified over silica gel (100% hexanes) to yield compound 4 (1.76 g, 7.2 mmol, 30% yield) as a colorless oil which was characterized using 1H NMR.

Fuente